Buying in Winter Garden: what it costs, what it rents for, how fast it sells

Winter Garden in twelve figures

Everything below comes from our own monthly tracking of 135 Florida areas. Nothing on this page is an estimate we made up, and nothing is a listing.

Figure	July 2026
Median sale price	$599,867
Price per square foot	$256
Typical rent	$2,308 a month
Gross yield, our arithmetic	4.62%
Property tax on the median home	$10,444
Days on market, median	39
Months of supply	4.4
Share of the asking price received	97.8%
Listings that cut the price	36.2%
Active inventory	1,383
New listings	774
Closings	550

If you are buying to live here

The median home is $599,867 against $488,142 across the areas we track. On property tax alone that median home pays $10,444 a year in Orange — $870 a month, inside the mortgage payment.

The market here is roughly balanced: 4.4 months of supply, close to the six that mark the balance. And it is fast: 39 days is well under the 72-day median. A house priced right does not sit here. Sellers are getting 97.8% of what they ask, and 36.2% of listings cut the price before they sell — which is the number that tells you whether an offer below asking is an insult or a conversation.

If you are buying to rent

Typical rent is $2,308 a month, which on the median price is a gross yield of 4.62%. The median across the areas we track is 5.72%. What you are buying here is not cash flow.

Gross is not net. Take the $10,444 of property tax off first and the yield is already down to 2.88%, before insurance, the association, vacancy or a single repair. That is the arithmetic the rental yield guide works through, and it is why a headline yield is a screening tool and not a decision.

If you are selling in Winter Garden

The median home takes 39 days to sell and collects 97.8% of its asking price. With 1,383 active listings against 550 closings in the month, that is 4.4 months of supply.

36.2% of listings here cut the price before selling. A price cut is what happens when the first number was wrong, and it costs more than the cut itself: a listing that has been sitting invites a lower offer.

New construction in Winter Garden

Our catalogue has 2 new-construction communities in Winter Garden, starting at $424,990.

New construction competes with the resale market in the same area, and the comparison is not only price: a new house carries an HOA fee and often a CDD assessment that an older one does not. The full catalogue lists what each community publishes.

Other areas in Orange

Same county, different numbers. These are the other ones we cover in depth:

Apopka.

How this page was built

Median sale price, price per square foot, days on market, months of supply, inventory, new listings, closings, the share of the asking price received and the share of listings that cut it: Redfin Data Center, July 2026. Typical rent: Zillow. Gross yield and the property tax figure are our own arithmetic on those inputs — rent times twelve over price, and the county millage from the Florida Department of Revenue applied to the median value with the homestead exemption. Refreshed every month, and the month is printed above so you can see how old it is. This page has no listings on it and is not an offer.